Hydrocarbon mercury salt of a fatty acid



Patented Mar. 12,1935 1,993,773

UNITED STATES PATENT OFFICE HYDROCABBON MERCURY SALT OF FATTY ACID Max Engelmann and Albert L.-Flenner, Wilmington. Del., assignors to E. L du Pont de Nem'ours & Company, Wilmington, Del a corporation of Delaware No Drawing. Application July 28, 1932,

Serial N0. 625, 26

7 Claims. (01. 260-13) all! tobject of this invention is the reaction Example 3 pr no of a non-substituted hydrocarbon mercury compoundand a salt of a higher fatty acid 313 Parts of phenyl mercury hydroxide m5- derived'from a saponifiable fator oil. f m m of are new 5 We have found that these new compounds can tm'hzed wlth 32.13% of 981mm After the 5' be produced by neutralizing hydrocarbon mercury methyl alcohol evaporated unqer reduced t hydroxides with fatty acids, such for example as sure the Phenyl Palmltate e of the e Out. has)! melting 01 56 C. is inseries, or the like, or by double exchange of the soluble in e? but very Soluble organic 10 organic mercury salts with metal salts of fatty Vents and i and vegetable 10v acids. We have also found suitable for this pur- In simflar manner many other mm pose other fatty acids derived from a saponiflable these senes may be produced fat or oil, such as for example, erucic, llnoleic. other hydmbqn mercury ricinoleic, alaesteric, lauric, and semunds- F i time which hydm l5 bacic acids. In fact, any fatty acid derived from radlcal i butyl' prowl and ml a We fat or on may be used in their various isomeric forms, maybe used, as

These new compounds have been found to be wen as cont'mnmg the tolyl" 1571 and very eflective as disinfecting agents and unlike 'mphthyl rams other hydrocarbon mercury salts, such for ex- These may be pmduoed in 20 ample, as the chlorides, sulfates acetates etc" suitable as dust by a one-step procg they are soluble in vegetable or mineral oils. For ess i F m 2 this reason these new compounds are especially ponents m hqmd'medmm by 51mph bnngmg adapted for use in having mineral the materials of the reaction into intimate conoils as a constituent, and therefore are useful in tact in a dry state and preferably in the pres cases wherebesides a a ti ence 0L8 solid diluent such as, 25

an insecticidal efie t is desired. some form of inert materials. The mercurizing- Th following examples m methods of reaction takes place in the absence of any added manufacturing our new compounds but it is to liquid fluent and gives directly in dust mm the be understood that these are illustrative only fatty acid salt of h non-substituted hydrocarand that other methods will be apparent from mercury y x de- 30 the discl r herein t Illustrative examples of the one-step dry process are as follows:

Example 1 I v Example 4 p 31.3 parts of ethyl mercury hydroxide dis- 35 solved in 100 parts of methyl alcohol are new 30 Parts of thyl mercury m 1 P r Of tralized with 37.6 g. of stearic acid, and arm d sodium 'palmitate, and 939 parts of talc are for five minutes. The methyl alcohol is evapo-' mundin t foul rated on a water bath. After cooling-down, the

40 ethyl mercury steal-ate crystallizes out in flaky Example 5 40 -crystalswhichareverysimilarinappearancetostearic acid; It has c. melting point of 12 c. It Parts of mercury-Oxide, M 0! Oleic is insoluble i water t very soluble in m n acid, 24.5 parts of tetra ethyl lead. and 357.4

ether, mineraloilaetc. parts of oil are mixed together and 'warmedat60'C.underagltationforabout245 Emmple 2 hours. Onepartofthismixhxrecontalningethyl mercuryoleateaddedtoiioopartsofwaterand 31.3 parts of ethyl mercury hydroxide are 2 parts of sodium carbonate givesa stable emul-.

mixed with 37.3 parts of oleic acid and warmed slonwhichcanbeusedfortheoontroloffungns, for five minutes on a water bath. After cooling 'diseasea-and, on account of its content of min- 50 down and standing for a-few hours, the ethyl eral oil, also for the control of insect pests, and mercury oleate-erystallizes out. It has a melting topreventtheirattackonseedsandplants. nus point of 62 C. The new compound-is insoluble emulsionis also very eflective for the control of a in 'water but very soluble in alcohol, acetone, sapstainof lumbenandlike ofcellulose t5 benaeneetherandmineraloils. products.

h Example 8 16.35 parts of mercury oxide, 432 parts of stearic acid, 1225 parts of tetra ethyl lead; and 928.2 parts of are milled together for 20 hours. The finished dust. containing ethyl mercm-y-stearate as the active ingredient, can be 30.4 parts of sodium oleate are heated in 400 parts of absolute alcohol for 15 m. on the boiling water bath. After-cooling to room temperature, the sodium chloride is filtered oil and the alcohol evaporated on the water bath. The phenyl mercury oleate remains as a very viscous oil. It is soluble in alcohol, acetone, mineral and vegetable oils, insoluble in water.

By the term dry process" as used herein, it'

istobeunderstood thatthematerialsaretobe used in their commercially available form containlngonlythesmallpercentageofwaterasis present under normal conditions.

It is to be understood that the foregoing examples are illustrative only and that our inven tionistobelimited onlyasindicatedinthe following patent claims:

We claim:

1. The reaction product of a non-substituted hydrocarbon mercury compound and a salt of a higher fatty acid of a saponiflable fat. 2. Ethyl mercury oleate.

3. Ethyl mercury stearate.

4. Ethyl mercury palmitate.

- 5. The process of producing a fatty acid salt of a non-substituted hydrocarbon which comprises reacting an allwl mercury compound and a salt of a higher fatty acid of a saponiflable fat.

6; The process of producing a fatty acid salt momma.

ALBERT L. mm.

oisoL'AlmzR '1,993,776.Maa: E elmann ahd Albert L. Flnner, Wilmifigton, Del. HYDROCARBON MERCURY ALT OF A FATTY ACID. Patent dated. March 12, 1935. Disclaimer filed November 10, 1939, by the assignee, E. I du Pont de Nemours and C'ompqny. t

Herb enters this disclaimer as to claim 1 of the said patent.

[ flicial Gazette December 5, 1989.] 

